Porto at sunset from the bridge

How To Choose A Travel Destination Everyone Loves

Have you ever taken a vacation that you thought would be a dream trip and the kids were dragging their feet and complaining the whole time? Or you plan an epic adventure with your partner and they end up not loving it as much as you do? I made these rookie mistakes a few times. Finally after years of being the trip planner in the family, I have figure it out and I’m ready to share it with you. Here are my tips on how to choose a travel destination that everyone loves.

Some of the links on this post are affiliate links. When clicking on the links and booking travel, I receive a small commission with no extra costs for you. Please note, I only recommend brands I actually use and trust. Please see full disclosure here.

Talk It Out: Good Communication Is Key

Tre Cime - one of the best hikes in the Dolomites

In order to choose a destination that is a big win for everyone, you have to communicate. Having one person plan the whole trip is nice for the others. It is sometimes great for you too. You can do what you want. However, this won’t work unless you talk to each other about how you want the trip to go and what you want to do.

Our summer trip of 2024 is a perfect example of this. I planned this whole trip. Mike was extremely busy with his new job and didn’t have time to do much of anything. I mentioned if he was okay with this or that, and he said, yes I trust you.

It was very nice of him to trust me and normally this would work out. I have traveled with my kids and husband for years and know what they like. What I didn’t understand at the time was his new needs. He was going to have to work while we were on our trip and while I knew that, I didn’t understand how much and how this would effect what he wanted to do after work.

I was under the impression that he would work a few hours in the morning and then spend the rest of the time exploring. That is how I planned the first part of the trip to Montenegro. Unfortunately, he burnt out quickly. 

By the time we got to Albania, he was behind and worked almost the whole time we were on the beach. I don’t think he ever went swimming. If I look back on that trip, I love the places we visited and really enjoyed the trip. If I ask him, he would say it was one of the most miserable trips he’s ever taken. 

In retrospect, I should have asked more questions about how long his job would take, and he should have been more upfront about how he was going to want to relax or only do something small in the evenings. 

Throughout the whole trip planning process, communication is an overarching thing that needs to happen.

I plan trips for my clients and communication is the most important part for me. There’s no way I could do my job without it. 

Want someone to help create your vacation itinerary for you? I can help. For destinations I have visited, I create personalized itineraries based on your interests using my expertise. Click here to send me a quick note saying where you’d like to go, and I’ll let you know if I can help you.


Tips For Choosing A Destination

There are two considerations that I prioritize when choosing a travel destination. The first is budget and the second is your time. 

The budget is huge because some trips cost way more than others. If your budget for a family of 4 is $4000, then a trip to Japan is out of the question. Your flights would take up a big chunk if not all of your budget. 

Whereas this February, we have a ski trip to Slovenia planned and our budget is $4000. Since we are coming from the Netherlands, this trip is within our budget.

Need help figuring out a travel budget? Use this post to help you: How To Make A Travel Budget And Helpful Tips To Save Money

Time is another consideration too when choosing a travel destination. Some trips just take more time to plan and get ready for. An international trip, for example, takes a little more coordination than a domestic trip where you are already familiar with how everything from hotels to parking work. 

After you look at those two huge considerations, how you choose a travel destination comes down to the following factors.

A Domestic Travel Vs An International Trip

Looking at your budget and your time, narrow down if you want to travel domestically or internationally. 

Choose a domestic trip if you are low on time and budget. Even if your budget isn’t a concern, time is the biggest factor to choose a domestic trip. It just is so much easier to plan. 

If you still want to travel internationally, but don’t have the time to plan the trip, you can hire someone to do this for you. 

I specialize in creating personalized itineraries for trips to the Netherlands and the surrounding countries. I can also help you plan trips to a few locations in the U.S. like Michigan, Colorado or Montana, as I’ve lived in all of these locations and am very familiar with them. 

While those are only a few locations, there are other companies that can help with this too. After deciding the location, you can find a company that will either do it all for you or plan a personalized itinerary for you.

If you have time to plan an international trip, I think it is worth it. Seeing more of the world has taught me and my kids so much about how others live. The values they have and cultural differences they’ve shown us are invaluable. 

You may also just want to travel domestically and that is okay too. If it is your first time traveling, choosing a location in your own country is easiest.

AirHelp+ 300X50

Next – What You Want To Do And See

Symphony of the Seas top deck in how to choose a travel destination

After you decide if your trip will be international or domestic, think about the activities you want to do. 

Many people jump right into picking the city, state or country. I want to visit Florida! But before picking a specific location, I would first look at what you want to do. 

  • Do you want to lounge on the beach at an all-inclusive resort where everyone serves you and attractions are at your finger tips?
  • Do you want to hike through slot canyons and red canyon walls? 
  • Do you want to ride a camel through the desert?
  • Are animals what you are searching for? Which animals in particular. 

Have a group discussion and come up with a list of things you’d like to do. Then compare what everyone wants to do. Is there a location that has it all? Maybe. Maybe not. 

How do you know if there is a travel destination that has everything on your list? This is one reason to use AI. Ask it something like, is there a place where I can swim with sharks, go hiking and relax on the beach? Give me 5 choices. I just asked this exact prompt to ChatGPT and it said:

  1. Hawaii
  2. Isla Holbox and Quintana Roo in Mexico
  3. The Bahamas
  4. Costa Rica
  5. The Azores

Not bad options!

Always remember there are always more trips that can be taken in the future. You won’t be able to go everywhere in one trip.

For example, Mike and I love getting out in the mountains. Hiking is always enjoyable and freeing for us. You ask our kids, they would say they hate it. They don’t, but for some reason they say that. *insert eye roll!*

So we compromise. For our trip to the Dolomites, we took the gondolas up to make it easier for their short legs. We also chose hiking trails that were easy to moderate and not too long.

It was also nice that it was in Italy, so we could bribe them with pizza at the hut mid-hike, or gelato when we got back to town. Those little things make it enjoyable for them. 

We also try to plan at least a few things that are specifically for them. We don’t fill the whole trip with kid-only activities because we wouldn’t enjoy the trip as much. At the same time, we make sure we don’t fill the whole trip with only our activities too. 

Cruise Critic

Narrow Down Your Travel Destinations Even More

Another consideration you don’t want to forget when picking a travel destination is the weather and the season. 

The Weather 

A few years ago we were looking for a hot place to visit to escape the winter weather. We didn’t want to travel far, so we were looking for a destination in Europe that would be warm in December. 

After searching various travel destinations, we didn’t find anywhere that would be over 70F (21C) degrees. While 70 is warm, it wasn’t warm enough for booking the trip we had envisioned. We wanted hot weather and a beach. 70 degrees didn’t quite give us what we were looking for.

Another example is a ski trip. Let’s say you are planning a ski trip to Colorado in December. The snowfall could be hit or miss. You wouldn’t want to plan a $10,000 dollar ski trip and not have great snow. 

Whereas if you planned that same trip in March, there is a greater likelihood that the mountain will be covered in powder. 

The Season

When I talk about seasons in this section, I’m actually not referring to summer, fall, wet or dry. I am speaking of travel seasons. It does have to do a little bit with the weather, but there’s more to it than that.

There is high season, low season and shoulder season. Each of these travel seasons refers to when tourists are most likely to visit that destination and yes, a lot of times that is when the weather is best. Other considerations though are the holidays or school breaks.

High Season

The high season is when there is the most agreeable weather in that destination; therefore, more tourists visit during that time. Other times when prices sky rocket are during school breaks and holidays like the end of December and the summer break. Easter time is also a big time for people to travel, especially in Latin America.

Traveling during high season has its positives and negatives. Some of the positives are that everything is open and the weather is enjoyable. The downside is that the crowds will be bigger and it will be more expensive. 

Low Season

Traveling during the low season is also a possibility. You may have to deal with some unpleasant weather. There’s also a chance that some attractions won’t be open or enjoyable.

I remember one instance when we were in Interlaken, Switzerland in March. We visited the tourism office asking about a waterfall that was nearby. They said it was closed. The waterfall. That made us giggle, but they just meant that the transportation to get there wasn’t running!

If you prefer those conditions to crowds of people and would like to save some money, it might be the way to go. 

Shoulder Season

The shoulder season is one of my favorite times to travel, especially to really popular vacation destinations. This is the time between high season and low season.

You can usually still get decent weather and the crowds have started to dissipate. It is also possible to save a bit of money on flights and hotels.


Summing Up How To Choose A Travel Destination

a woman and her son in front of the church on Our Lady of the Rocks in Kotor Bay

After considering your budget, the time you have to plan and coordinate the trip, if you want to travel domestically or internationally, the attractions and things you want to see and do, and the weather and season, I hope you have come up with a few fantastic options for travel destinations. 

Of all those options, there’s no wrong answer. Just keep communicating with each other while planning the itinerary. 

Need help with planning your trip. Take a look at this post I created that walks you through the steps. Easy Steps To Planning A Trip + A Bonus Checklist

Freebie: Travel Planning Checklist!

It includes:

  • An area to write your basic trip details including the destination, dates of your trip and your travel goal
  • A section to write an estimated budget for transportation, lodging, food, entertainment etc…
  • Spot for notes!
  • Checklist for the items you need to do before embarking on your trip. 
  • An additional checklist with international considerations if you are planning a trip abroad.

Leave a Comment

Your email address will not be published. Required fields are marked *

WordPress Cookie Plugin by Real Cookie Banner